Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to San José from $167

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 5/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$438Delta
Tue, Sep 22 - Wed, Sep 23
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 12:30 pm
SJO
-
MDW
22h 05m
2 stops
$443Delta
Tue, Sep 22 - Wed, Sep 23
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
Multiple Airlines Logo
1:00 pm - 11:09 am
SJO
-
MDW
21h 09m
2 stops
$455Multiple Airlines
Fri, May 8 - Mon, May 11
Delta Logo
6:23 am - 1:15 pm
MDW
-
SJO
7h 52m
1 stop
Delta Logo
1:20 pm - 8:43 am
SJO
-
MDW
18h 23m
2 stops
$465Delta
Sat, May 9 - Tue, May 19
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
9:00 am - 7:15 pm
SJO
-
MDW
9h 15m
1 stop
$476Southwest
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
9:05 am - 6:40 pm
MDW
-
SJO
10h 35m
2 stops
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$480Southwest
Tue, Sep 8 - Tue, Sep 15
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
Southwest Logo
9:00 am - 5:30 pm
SJO
-
MDW
7h 30m
1 stop
$484Southwest
Thu, May 14 - Tue, May 19
Southwest Logo
10:30 am - 6:40 pm
MDW
-
SJO
9h 10m
1 stop
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
$488Southwest
Wed, Sep 2 - Tue, Sep 8
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
Multiple Airlines Logo
1:00 pm - 10:02 pm
SJO
-
MDW
32h 02m
2 stops
$491Multiple Airlines
Fri, May 8 - Mon, May 11
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$493Delta
Wed, Sep 16 - Tue, Sep 22

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Sep 22
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
Sep 23
SJO1:25 pmSan José Juan Santamaria Intl
7h 21m
1 stop
MDW9:46 pmChicago Midway
$438
Delta
Sep 22
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
Sep 23
SJO1:25 pmSan José Juan Santamaria Intl
22h 05m
2 stops
MDW12:30 pmChicago Midway
$443
Delta
May 9
MDW6:23 amChicago Midway
7h 52m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
May 19
SJO1:20 pmSan José Juan Santamaria Intl
18h 23m
2 stops
MDW8:43 amChicago Midway
$465

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Sep 1
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Sep 15
SJO9:00 amSan José Juan Santamaria Intl
9h 15m
1 stop
MDW7:15 pmChicago Midway
$476
Southwest
Sep 8
MDW9:05 amChicago Midway
10h 35m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
Sep 15
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
$480
Southwest
May 14
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
May 19
SJO9:00 amSan José Juan Santamaria Intl
7h 30m
1 stop
MDW5:30 pmChicago Midway
$484

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-9:46 pm

1 stop7h 21m

$438

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-12:30 pm

2 stops22h 05m

$443

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 5/8

4:52 pm-3:18 pm

1 stop23h 26m

San José Juan Santamaria Intl

Mon 5/11

1:00 pm-11:09 am

2 stops21h 09m

$455

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 5/9

6:23 am-1:15 pm

1 stop7h 52m

San José Juan Santamaria Intl

Tue 5/19

1:20 pm-8:43 am

2 stops18h 23m

$465

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/1

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Tue 9/15

9:00 am-7:15 pm

1 stop9h 15m

$476

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/8

9:05 am-6:40 pm

2 stops10h 35m

San José Juan Santamaria Intl

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

$480

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 5/14

12:10 pm-7:00 pm

1 stop7h 50m

San José Juan Santamaria Intl

Tue 5/19

9:00 am-5:30 pm

1 stop7h 30m

$484

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 9/2

10:30 am-6:40 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 9/8

9:00 am-9:50 pm

2 stops11h 50m

$488

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 5/8

4:52 pm-3:18 pm

1 stop23h 26m

San José Juan Santamaria Intl

Mon 5/11

1:00 pm-10:02 pm

2 stops32h 02m

$491

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 9/16

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Tue 9/22

1:25 pm-9:46 pm

1 stop7h 21m

$493

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $513. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $689. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $514. Flights at noon are often more expensive with an average ticket price of $664.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 30m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 30m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 30m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,327 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Santa Elena
Dominical
San Gerardo de Dota
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your San José trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 5/26
Tue 6/2
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Costa Rica